John Gregory may have been connected in Britain with Mark and Thomas Gregory, a London firm that had entered the fur trade shortly after the conquest. He came to North America in 1773 and that year formed a partnership with the fur trader James Finlay, who had considerable experience in the field, having been one of the first British traders to reach the lower Saskatchewan River by 1766. Little is known of Gregory’s life as a trader, but he did spend some time on the Sturgeon River (Sask.). By the end of the 1770s he was displacing Finlay as the dominant partner; in 1777 Gregory invested £2,500 to Finlay’s £11,770, but the following year Gregory’s investment was £6,790 to Finlay’s £4,750, and in 1782 £15,805 to Finlay’s £750. Their efforts were concentrated primarily on Detroit (Mich.) and secondarily on Michilimackinac (until 1781 Mackinaw City, then Mackinac Island, Mich.). In 1783 Gregory made what appears to have been his largest investment, £18,460, of which £17,500 was in the Detroit trade.

After the retirement of Finlay in 1783 or 1784, Gregory formed a new partnership with Normand MacLeod*, who had connections at Michilimackinac; in 1784 they traded principally to that post, with a secondary interest in the Mississippi valley. That year two traders excluded from the North West Company during its reorganization in the winter of 1783–84, Peter Pangman and Peter Pond, persuaded Gregory, MacLeod and Company to move into the northwest trade. Pond opted finally to join the NWC, but Pangman and his associate, John Ross, were made wintering partners in Gregory, MacLeod, as was Alexander Mackenzie, a clerk in Gregory’s Montreal counting-house since 1779. Although Joseph Frobisher affirmed that Gregory, MacLeod furnished the backbone of the opposition to the NWC, the competition was unequal, the latter being larger, more experienced in the northwest trade, and better financed; in 1785 it sent 25 canoes to Grand Portage (near Grand Portage, Minn.) while Gregory, MacLeod could send only eight. By 1786 the challengers were in grave financial difficulty. That December their creditors chose from among themselves three trustees, Robert Ellice and Company, Richard Dobie, and Edward William Gray, to receive and distribute among them all returns of the next season’s trade. Moreover, rivalry with the NWC, always fierce, had become violent: in the summer of 1787 Gregory, who was attending his company’s annual general meeting at Grand Portage, was shaken when one of his clerks, Roderick McKenzie*, arrived unexpectedly with news of the murder of Ross by Pond’s men in the Athabasca country. When Simon McTavish of the NWC arrived at Grand Portage for its annual meeting, he proposed that Gregory, MacLeod join the NWC in order to avoid further bloodshed, an invitation that Gregory wisely realized could hardly be declined. By the agreement of entry later that year each partner in Gregory, MacLeod received a one-twentieth share in an expanded NWC. The competition had cost Gregory dearly, however; by 1792 he had still not discharged all the debts he had brought with him into the NWC and MacLeod was disclaiming all responsibility for them.

None the less Gregory soon achieved a certain prominence within the NWC. In 1790 he was named one of its representatives at the annual meetings at Grand Portage, where the wintering partners exchanged their furs for trade goods, and later that year he purchased MacLeod’s share in the company. He appears to have acquired the respect of McTavish, who on leaving for London in 1791 arranged secretly to entrust Gregory with control of the Montreal business during his absence, much to the chagrin of Frobisher; he complained that Gregory did not manifest sufficient regard for his experience and position as a senior partner. That year Gregory’s election to the Beaver Club, membership in which was limited to men who had wintered in the Indian country, signalled his acceptance within the NWC, for its members dominated the club and controlled entry into it.

In 1793 Gregory was apparently in charge of the hiring of traders, and, with William McGillivray*, was director of operations at Grand Portage. Two years later he was made a partner in McTavish, Frobisher and Company, the principal outfitting firm in the NWC; he was again to act as representative, with McGillivray and Mackenzie, at the annual meetings at Grand Portage. As well, he made numerous trips to New York to conduct negotiations for the shipping of furs to the Far East, an alternative to European markets disrupted by the Napoleonic Wars. In 1799 Gregory held two of the ten shares in McTavish, Frobisher, which had been reorganized following Frobisher’s retirement, and he was assigned the superintendence of the “Outfits Packing and Shipping Concerns.” When McTavish died in 1804, he bequeathed £100 to Gregory, his “friend and partner.” Later that year Gregory signed the agreement which brought to an end the competition in the northwest between the NWC and the New North West Company (sometimes called the XY Company) [see John Ogilvy]. On 31 May 1806 Gregory retired from McTavish, Frobisher and from the fur trade.

On 22 Feb. 1778 Gregory had married at Montreal Isabella Ferguson, and they had several children. Their three daughters were described as “very fine, lovely girls” by George Thomas Landmann*, a British officer, in 1799; the youngest, Maria, married the fur trader David Mitchell in 1806. A son, George, married Jane Prescott Forsyth, daughter of the Montreal merchant John Forsyth*.

It would appear that during the 1780s Gregory had begun spending most of his time in Montreal. He owned a stone house on Rue Saint-François, which he sold before June 1789, probably to McTavish, Frobisher; about 1799 he was living on Mount Royal next to McGillivray and Mackenzie. In 1787 he had been a member of a grand jury that complained of the inadequacy of Montreal’s jail and court-house. He was a staunch member of the Scotch Presbyterian Church, later known as St Gabriel Street Church.

In 1802 Gregory received, according to the system of township leaders and associates [see James Caldwell], 1,200 acres in Arthabaska Township; he soon added the grants of his associates to make a total of 11,550 acres. The same year, and in 1804, he bought several contiguous lots along the Chemin des Tanneries (Rue Carrière) at Montreal; there, in the woods on the bank of the Rivière Saint-Pierre, he built a manor-house called Woodland, from which a long poplar-lined drive was cut out to the road. Gregory died at Woodland at about age 66 on 21 Feb. 1817. He had been, according to the Montreal Herald, “one of our most respectable citizens.”

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